- 305-619-0140
Private Liveaboard Classes
Florida keys sailing, come sail with us.
Proud Member of the ASA
At Florida Keys Sailing our specialty is: Private Live Aboard Sailing Classes and Sailing Vacations with just you and your spouse or friends. “Learn to Sail” or take an Advanced Class to develop your skills. Qualified sailors can Charter our boats. A Captain will happily take you and your family on a Day Sailing Trip if you need one. Many sailing classes offered elsewhere crowd you on a boat with a group of total strangers.
At Florida Keys Sailing ALL of our Sailing Classes, Day Sailing Trips, and Private Charters are exactly that…PRIVATE.
No one else except YOUR Party is ever on-board. This means you will learn more by having more time DOING, not WATCHING someone else sail. Dollar for dollar you will find more VALUE in taking your Sailing Courses at Florida Keys Sailing.
Fun on the Waves
Our Classes
To learn more about the liveaboard classes we offer, visit our classes page
2 DAY BASIC FUNDAMENTALS OF SAILING
Designed for beginners who want the best introduction to the exciting sport of sailing. Students will receive a good understanding of all the “Basic Fundamentals of Sailing”. They will leave as very competent Crew Members.
3 DAY BASIC KEELBOAT “LEARN TO SAIL CLASS”
Beginner students will learn to responsibly be the Skipper of a Day Sailing Keelboat in familiar waters in moderate wind and sea conditions. Classes available are year round on demand based on your travel plans.
5 DAY BASIC COASTAL CRUISING OR 101 & 103
Students will learn to responsibly skipper and crew an auxiliary powered cruising sailboat during daylight hours within sight of land in moderate wind conditions. This Private Live Aboard Class is taught aboard our Catalina 30' or Irwin 34 Offered all year on demand based on your travel plans.
5 DAY BAREBOAT CRUISING OR 103 & 104
Charter a cruising sailboat during daylight hours in most wind and sea conditions. This Private Live Aboard Class is taught aboard our Irwin 34. Offered all year on demand based on your travel plans. 5 Days and 4 Nights…Privately Living aboard at our Dock
3/1 DAY ADVANCED COASTAL CRUISING OR 106
Cruise a sailboat during nighttime hours in most wind and sea conditions. A Private Live Aboard Class is held aboard our Catalina 30 or Irwin 34. Offered all year on demand based on your travel plans. 3 Days and 3 Nights…Privately Living Aboard
7 DAY BAREBOAT CRUISING OR 101, 103 &104
Charter a cruising sailboat during daylight hours in most wind and sea conditions. This Private Live Aboard Class is taught aboard our Irwin 34 This is the Class the Bareboat Charter Companies want you to have. Offered all year long on demand based on your travel plans. 7 Days and 6 Nights…Privately Living Aboard at our Dock
3 DAY FAST TACK TO CRUISING ASA 101 & 103
It’s the fastest and least expensive way to get the first 2 – ASA Certifications. Both combined into a 3 Day / 2 Night Live aboard Class. Prior sailing experience before enrolling is advised.
5 - DAY FAST TACK TO BAREBOAT CRUISING ASA 101, 103 & 104
It’s the fastest and least expensive way to get these 3 - ASA Certifications. All 3 are combined into a 5 Day / 4 Night – Live aboard Class. Prior sailing experience before enrolling is advised. A second student enrolls for FREE!
Testimonials
Daysailing & charters, we offer both daysailing and charters, click below to learn more.
- SAILING LOCATION: Keys Fisheries & Marina 35th St Gulfside, MM 49 Marathon, FL 33050
- By Mail: Florida Keys Sailing 5171 Overseas Hwy #504407 Marathon, FL 33050
- By E-Mail: [email protected]
- By Telephone: 305-619-0140
- Marathon Chamber of Commerce
- Get Knotted - Animated Knots
- Sombrero Lighthouse Data and Marine Forecast
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Key West, FL
boating guide
In addition to the best offers we have for boat and yacht charters in Key West, FL, see also options available for rent in these nearby locations:
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Discover Key West, FL with Sailo - a gorgeous boating playground for you to enjoy!
Ready to see your options for renting a sailboat in key west, fl, learn how to find the perfect yacht for you, how much is it to charter a key west, fl yacht for a day, what is sailo’s cancellation policy, sustainable yachting tips.
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Introducing Vivo Per Lei 58 Leopard Catamaran flagship model Learn More
Creating unforgettable journeys on custom designed luxury catamarans learn more, luxury catamaran sailing charters tailored in every way to suit your needs learn more, key west and key largo locations sailing the beautiful florida keys, bahamas and beyond learn more, catamaran sailing charters half day, full day & overnight learn more, welcome to calypso sailing.
Calypso Sailing was established in 1988 in the beautiful Florida Keys. With locations in both Key Largo and Key West we specialize in luxury sailing vacations on a range of Leopard Catamarans, both bareboat and Captained. Our monohull sailing charters can take groups of 6 to 38 on day, sunset and overnight trips whilst not forgetting the iconic African Queen steamboat from the 1951 movie starring Humphrey Bogart and Katharine Hepburn which operates daily in Key Largo.
Our aim is taking care of all your cruising needs
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